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Hello @jr-schwartz, thank you for bringing this up in the community. When you attempt to sync with your bank, are you getting any errors? This will help me determine if this is a known issue or not. Here is an article to help with manually adding those transactions into your account while we figure this out: Import bank transactions using Excel CSV files.
It's also beneficial to go through some browser troubleshooting as well. Let's start with these steps:
Lastly, let's try to disconnect and reconnect the bank:
Reconnect the account:
I'm looking forward to hearing from you. You can just reply to this thread and I'll be here to help you out. You can also let us know if you have any other issues or questions as well.